PROSTAGLANDINS AND CONGENERS .28. SYNTHESIS OF 2-(OMEGA-CARBALKOXYALKYL)CYCLOPENT-2-EN-1-ONES, INTERMEDIATES FOR PROSTAGLANDIN SYNTHESES
PROSTAGLANDINS AND CONGENERS .28. SYNTHESIS OF 2-(OMEGA-CARBALKOXYALKYL)CYCLOPENT-2-EN-1-ONES, INTERMEDIATES FOR PROSTAGLANDIN SYNTHESES
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DOI：
10.1021/jo01311a032
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发表时间：
1980-01-01
影响因子：
3.6
通讯作者：
WEISS, MJ
中科院分区：
文献类型：
--
作者：
BERNADY, KF;POLETTO, JF;WEISS, MJ
本文介绍了一种合成2-取代环戊烯酮前体的方法，该前体是通过共轭加成法制备11-脱氧野牡丹素所必需的。在如此制备的环戊烯酮中，有一些具有设计用于抑制或防止脂肪酸β-环戊烯酮的特征。最终前列腺素类似物的氧化代谢。这些特征包括α位的甲基、乙基、苯基和氟取代基。脂肪酸侧链的位置和β-具有O2、S或偕-二甲基亚甲基部分的亚甲基。制备了侧链长度为2-9个碳原子的环戊烯酮。
A methodology is described for the synthesis of the 2-substituted cyclopentenone precursors required for the preparation of 11-deoxyprostaglandins by the conjugate addition procedure. Among the cyclopentenones so prepared were some with features designed to inhibit or prevent fatty acid .beta.-oxidative metabolism of the ultimate prostaglandin analog. These features include methyl, ethyl, phenyl and fluorine substituents at the .alpha. position of the fatty acid side chain and replacement of the .beta.-methylene group with O2, S, or gem-dimethylmethylene moieties. Cyclopentenones with side chains varying in length from 2-9 C atoms were prepared.